One More Chance

by Heathen57

Caution: This Romantic Sex Story contains strong sexual content, including Ma/Fa, Consensual, Romantic, .

Desc: Romantic Sex Story: Karen had broken Bill's heart in High school. He had gotten over her until she contacts him. Will he take one more chance? Based on real life events.

Here I am, sitting in business class, on a 727 heading to Portland. This is just a normal business trip, clients to wine and dine, deals to close. Yet, I am nervous. I open the book I brought along, trying to lose myself for a while in a world where others are the focus of indecision and strife. I read the same paragraph three times and still cannot comprehend the words. With a sigh, I set their world aside, picked up my laptop and returned to my own indecision.


Could I come and see you next time you are in the area? I really need to talk face to face.


I had already answered her, telling her I would call on the next trip and let her know where I was staying; offering her dinner and a chance to talk. We had not seen each other face to face in more than 15 years. After all this time, why was she so insistent that we meet? I was content with how things had been between us. If I was honest with myself, I could admit I wasn't happy about it, but I had come to accept it.

I drifted back to the time when I had first met Karen. I hung out with the other car nuts during high school. I had a black and red GTO that used up most of the paychecks I had from my part time job. Karen was a friend of another member of the group. A bit of a wild child, she just hung out on the fringes.

It took awhile, but we became friends. I got to know her better. She had a troubled family life and being the way I was, I took it on myself to make her life a little happier. We started to hang around in school. I picked her up every morning and gave her a ride. I was quietly falling for her, but was too shy to say anything. She was interested in Darren, a guy that had dropped out earlier that year.

We continued this way until a little before Thanksgiving. I headed down the road to pick her up and found her sitting at the end of her driveway with a suitcase. When she opened the door, I could see her eyes were all red and puffy. The streaks of her tears had run down her beautiful face.

"Mama threw me out this morning. I can't go back, and she won't let me see my sister."

That was all she got out before she broke down again. We didn't make it to school that day, but went to a park where I just held her. She finally asked to go to a girlfriend's house. Sandy said she could stay. I didn't feel right about it, but left her there anyway.

Things went badly for Karen for a while. Her mother reported her as a runaway and the police picked her up at Darren's house. Placed in a group home, she was to continue going to school. I would leave for school early, go and pick her up, so she would have a ride. I bought silly cards for her to cheer her up. I did anything I could do to make her life easier. I was falling for her more and more.

Any hope I had came crashing down the day she asked if I would drop her off somewhere other than the group home. With her giving directions, we finally pulled up to a driveway. Darren walked out of the garage as she stepped out of the car. She ran up to him and when they kissed, my heart fell to my feet. I just drove off, my heart breaking.

I put up a good front and continued to take her to school, but it was draining on me. She was giving Darren what I so desperately wanted. I know she felt the distance that I put between us, but she didn't say anything.

She finally moved to the West coast. I didn't see her off. Darren was going to take her to the airport. I just couldn't take that pain. Karen had left, but in some destructive way, I missed her.

Now I had to decide if I wanted to open up those wounds again. I had closed that part of my past for years until I received an email on my personal account:

Mr. Gilliam,

Are you the same Bill Gilliam that went to Franklin High School in 1975 and drove a red Pontiac? If you are, please reply. I have thought about you a lot through the years.


I answered it before I even thought about it. I probably should have ignored it, but something made me go ahead and write a reply. The emails flew back and forth as we told each other about our lives. I was still single and she was married, but having trouble with her husband. When I mentioned that I would be off-line for a week for a business trip, she wrote that she had to see me. The same email I had been staring at for almost an hour.

I checked into the hotel in Portland, unpacked, and then called to confirm the first appointment for Monday. Since it was Friday, I had the weekend to look around. I thought about going to get some dinner, but instead sat staring at the phone. I finally dialed the number Karen had given me.

On the third ring, I heard a soft voice say "Hello?"

"Is this Karen?"

"Oh God, is that you Billy?"

"Yeah it's me. How you doing?"

"I'm okay. Does this mean you are in Portland?"

"Sure am. You said you wanted to have dinner. Would you like to meet tonight at 7? We can eat at the restaurant just off the lobby."

"Seven's great. I'll be there. Billy? I have really missed you."

"Me too. I'll see you at 7 then."

I had 2 hours so I took a shower and then dressed for dinner. I wasn't sure what I was expecting, but I did know that I wasn't going to have my heart broke again.

I stepped off the elevator and there she was, standing in the lobby watching the other guests as they milled about. Her hair was now shoulder length, but she still had the same beautiful face. He body, wrapped in an evening gown of blue satin, had matured, gaining fuller curves and making her even sexier than before.

While I was musing about the changes, she spotted me. Almost running, she crossed the space between us and wrapped me in a bear hug.

"Billy, it is so good to see you again. I missed you so much when I left."

I returned the hug, very aware of the firmness of her body against mine. I untangled myself before my erection became an embarrassment to us both. Holding her at arms length, I looked down then back up until I was looking in her eyes.

"You are as pretty as ever."

She looked down and whispered a quiet "thanks". Taking her arm, I led her to the restaurant, catching the envious looks of the other male guests. They seated us in a quiet booth and left us to look over the menu. Dinner was good, and we made light conversation until we were finishing up our coffee.

"How about we get out of here and find some place we can talk. I want to know what has been going on."

My little head had an answer in place: up to my room so I could fuck her brains out. The big head prevailed and I suggested we take a walk around the area. As we headed out, she reached out and took my hand. I felt a jolt going straight through me. Her hand, small and soft, seemed to match mine perfectly. I kept telling myself I was not going to become involved. Unfortunately, that resolve was slipping.

As we walked, she told me that she and her husband had separated and that he had left for California. She knew he had been, in her words, "fucking that blonde haired cunt from the coffee shop" and that they had left together. She was still working in the real estate market.

I told her of my rise in our software company and what I was doing out here. We headed back to the hotel and, at her request, my room. Once inside, I draped my jacket over a chair and offered her a drink. I finally settled on the couch and she took the chair closest.

We talked a little more of the people we both knew in school. Finally she asked, "Did you ever hear what happened to Darren?"

I stopped for a second. "I thought you kept up with him." I tried, but the strain in my voice came out.

She looked confused. "After I left, I never heard from him."

"Last I heard he was busted for carjacking and assault."

"I'm sorry to hear that, but he was headed that way. He was either drunk or stoned most of the time."

I only mumbled an agreement and took another drink. My glass was empty, so I went to the bar and refilled it. When I got back, Karen was looking at me closely.

"Billy, just before I left, you were so distant. I felt so lost. Can you tell me what went wrong?"

I tried to just gloss it over, but she would not let it rest. Finally I just let it out.

"I just couldn't take watching you and Darren together. Taking you to his house and watching you two kissing, his hands pawing your boobs and your ass, just tore me up. I couldn't take it anymore."

The shock on her face was evident. I was on a roll though and the words just kept on tumbling out without my brain doing a check first.

"I am... I mean, I was madly in love with you. When I thought about him having your body, I was sick. I gave up."

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Story tagged with:
Ma/Fa / Consensual / Romantic /